US2005245529A1PendingUtilityA1
Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds
Est. expiryApr 14, 2024(expired)· nominal 20-yr term from priority
Inventors:Dirk StenkampStephan Georg MuellerPhilipp LustenbergerThorsten Lehmann-LintzGerald Juergen RothKlaus RudolfMarcus SchindlerLeo ThomasRalf Lotz
C07D 401/14C07D 401/10C07D 213/30C07D 213/38C07D 471/08
44
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Claims
Abstract
Alkyne compounds of formula I wherein A, B, W, X, Y, Z, R 1 , and R 2 have the meanings given herein, which have MCH-receptor antagonistic activity and are useful for preparing pharmaceutical compositions for the treatment of metabolic disorders and/or eating disorders, particularly obesity and diabetes.
Claims
exact text as granted — not AI-modified1 . A compound of formula (I)
wherein:
R 1 and R 2 are each independently H, C 1-8 -alkyl, C 3-7 -cycloalkyl, or a phenyl or pyridinyl group optionally mono- or polysubstituted by identical or different groups R 20 and/or monosubstituted by nitro, wherein the alkyl or cycloalkyl group is optionally mono- or polysubstituted by identical or different groups R 11 , and a —CH 2 — group in position 3 or 4 of a 5-, 6-, or 7-membered cycloalkyl group is optionally may be replaced by —O—, —S—, or —NR 13 —, or
R 1 and R 2 form a C 3-8 -alkylene bridge, wherein a —CH 2 — group not adjacent to the N atom of the R 1 R 2 N— group is optionally replaced by —CH═N—, —CH═CH—, —O—, —S—, —SO—, —(SO 2 )—, —CO—, —C(═CH 2 )—, or —NR 13 —, wherein in the alkylene bridge one or more H atoms are optionally replaced by identical or different groups R 14 , and the alkylene bridge is optionally substituted by one or two identical or different Cy groups such that the bond between the alkylene bridge and the group Cy is made via a single or double bond, via a common C atom forming a spirocyclic ring system, via two common adjacent C and/or N atoms forming a fused bicyclic ring system, or via three or more C and/or N atoms forming a bridged ring system;
X is a C 1,6 -alkylene bridge independently substituted by one or more substituents selected from fluorine, chlorine, hydroxy, cyano, CF 3 , C 1-4 -alkyl, hydroxy-C 1-4 -alkyl, C 3-6 -cycloalkyl, and C 1-4 -alkoxy, wherein two alkyl substituents thereof are optionally joined together to form a C 3-7 -cycloalkyl group, or
a C 2-4 -alkylenoxy or C 2-4 -alkyleneimino bridge, wherein the imino group is optionally substituted by a C 1-4 -alkyl group, and wherein the alkylene unit is independently substituted by one or more substituents selected from fluorine, chlorine, CF 3 , hydroxy-C 1-4 -alkyl, C 1-4 -alkyl, and C 3-6 -cycloalkyl, wherein two alkyl substituents thereof are optionally joined together to form a C 3-7 -cycloalkyl group or a cyclo-C 4-6 -alkyleneimino group, or
a C 3-6 -alkenylene or C 3-6 -alkynylene bridge optionally independently substituted by one or more substituents selected from fluorine, chlorine, CF 3 , hydroxy-C 1-4 -alkyl, C 1-4 -alkyl, and C 3-6 -cycloalkyl, wherein two alkyl substituents thereof are optionally joined together to form a C 3-7 -cycloalkyl group or C 5-7 -cycloalkenyl group;
W and Z are each independently a single bond or a C 1-2 -alkylene bridge, while two adjacent C atoms are optionally joined together with an additional C 1-4 -alkylene bridge, and one or two C atoms are optionally independently substituted by one or two identical or different C 1-3 -alkyl groups, wherein two alkyl groups are optionally joined together to form a carbocyclic ring;
Y and A are each independently phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, naphthyl, tetrahydronaphthyl, indolyl, dihydroindolyl, quinolinyl, dihydroquinolinyl, tetrahydroquinolinyl, isoquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl, benzimidazolyl, benzoxazolyl, chromanyl, chromen-4-onyl, thienyl, furanyl, benzothienyl, or benzofuranyl, each optionally mono- or polysubstituted at one or more C atoms by identical or different groups R 20 , in the case of a phenyl ring, additionally optionally monosubstituted by nitro, and/or one or more NH groups are optionally substituted by R 21 ;
B is independently Y, A, or C 1-6 -alkyl, C 1-6 -alkenyl, C 1-6 -alkynyl, C 3-7 -cycloalkyl, C 5-7 -cycloalkenyl, C 3-7 -cycloalkyl-C 1-3 -alkyl, C 3-7 -cycloalkenyl-C 1-3 -alkyl, C 3-7 -cycloalkyl-C 1-3 -alkenyl, or C 3-7 -cycloalkyl-C 1-3 -alkynyl, wherein one or more C atoms are optionally independently mono- or polysubstituted by halogen and/or optionally monosubstituted by hydroxy or cyano and/or cyclic groups are optionally mono- or polysubstituted by identical or different groups R 20 ;
Cy is a saturated 3- to 7-membered carbocyclic group, an unsaturated 4- to 7-membered carbocyclic group, a phenyl group, a saturated 4- to 7-membered or unsaturated 5- to 7-membered heterocyclic group with an N, O, or S atom as heteroatom, a saturated or unsaturated 5- to 7-membered heterocyclic group with two or more N atoms or with one or two N atoms and an O or S atom as heteroatoms, or an aromatic heterocyclic 5- or 6-membered group with one or more identical or different heteroatoms selected from N, O, and/or S, wherein the saturated 6- or 7-membered groups thereof are optionally bridged ring systems with an imino, (C 1-4 -alkyl)-imino, methylene, (C 1-4 -alkyl)-methylene, or di-(C 1-4 -alkyl)-methylene bridge, and the cyclic groups thereof are optionally mono- or polysubstituted at one or more C atoms by identical or different groups R 20 , in the case of a phenyl group optionally additionally monosubstituted by nitro, and/or one or more NH groups are optionally substituted by R 21 ;
R 11 is halogen, C 1-6 -alkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, R 15 —O—, R 15 —O—CO—, R 15 —CO—O—, cyano, R 16 R 17 N—, R 18 R 19 N—CO—, or Cy, wherein one or more C atoms thereof are optionally independently substituted by halogen, OH, CN, CF 3 , C 1-3 -alkyl, or hydroxy-C 1-3 -alkyl;
R 13 is independently R 17 ;
R 14 is halogen, cyano, C 1-6 -alkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, R 15 —O—, R 15 —O—CO—, R 15 —CO—, R 15 —CO—O—, R 16 —R 17 N—, R 18 R 19 N—CO—, R 15 —O—C 1-3 -alkyl, R 15 —O—CO—C 1-3 -alkyl, R 15 —SO 2 —NH—, R 15 —O—CO—NH—C 1-3 -alkyl, R 15 —SO 2 —NH—C 1-3 -alkyl, R 15 —CO—C 1-3 -alkyl, R 15 —CO—O—C 1-3 -alkyl, R 16 R 17 N—C 1-3 -alkyl, R 18 R 19 N—CO—C 1-3 -alkyl, or Cy—C 1-3 -alkyl;
R 15 is H, C 1-4 -alkyl, C 3-7 -cycloalkyl, C 3-7 -cycloalkyl-C 1-3 -alkyl, phenyl, phenyl-C 1-3 -alkyl, pyridinyl, or pyridinyl-C 1-3 -alkyl;
R 16 is H, C 1-6 -alkyl, C 3-7 -cycloalkyl, C 3-7 -cycloalkyl-C 1-3 -alkyl, C 4-7 -cycloalkenyl, C 4-7 -cycloalkenyl-C 1-3 -alkyl, ω-hydroxy-C 2-3 -alkyl, ω-(C 1-4 -alkoxy)-C 2-3 -alkyl, amino-C 2-6 -alkyl, C 1-4 -alkyl-amino-C 2-6 -alkyl, di-(C 1-4 -alkyl)-amino-C 2-6 -alkyl, or cyclo-C 3-6 -alkyleneimino-C 2-6 -alkyl;
R 17 is independently R 16 or phenyl, phenyl-C 1-3 -alkyl, pyridinyl, C 1-4 -alkylcarbonyl, hydroxycarbonyl-C 1-3 -alkyl, C 1-4 -alkoxycarbonyl, C 1-4 -alkoxycarbonyl-C 1-3 -alkyl, C 1-4 -alkylcarbonylamino-C 2-3 -alkyl, N-(C 1-4 -alkylcarbonyl)-N-(C 1-4 -alkyl)-amino-C 2-3 -alkyl, C 1-4 -alkylsulfonyl, C 1-4 -alkylsulfonylamino-C 2-3 -alkyl, or N-(C 1-4 -alkylsulfonyl)-N(—C 1-4 -alkyl)-amino-C 2-3 -alkyl;
R 18 and R 19 are each independently H or C 1-6 alkyl;
R 20 is independently R 22 or halogen, hydroxy, cyano, C 1-6 -alkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, C 3-7 -cycloalkyl, C 3-7 -cycloalkyl-C 1-3 -alkyl, hydroxy-C 1-3 -alkyl, or R 22 —C 1-3 -alkyl;
R 21 is C 1-4 -alkyl, ω-hydroxy-C 2-6 -alkyl, ω-C 1-4 -alkoxy-C 2-6 -alkyl, ω-C 1-4 -alkyl-amino-C 2-6 -alkyl, ω-di-(C 1-4 -alkyl)-amino-C 2-6 -alkyl, ω-cyclo-C 3-6 -alkyleneimino-C 2-6 -alkyl, phenyl, phenyl-C 1-3 -alkyl, C 1-4 -alkyl-carbonyl, C 1-4 -alkoxy-carbonyl, C 1-4 -alkylsulfonyl, aminosulfonyl, C 1-4 -alkylaminosulfonyl, di-C 1-4 -alkylaminosulfonyl, or cyclo-C 3-6 -alkylene-iminosulfonyl;
R 22 is pyridinyl, phenyl, phenyl-C 1,3 -alkoxy, cyclo-C 3-6 -alkyleneimino-C 2-4 -alkoxy, OHC—, HO—N═HC—, C 1-4 -alkoxy-N═HC—, C 1-4 -alkoxy, C 1-4 -alkylthio, carboxy, C 1-4 -alkylcarbonyl, C 1-4 -alkoxycarbonyl, aminocarbonyl, C 1-4 -alkylaminocarbonyl, di-(C 1-4 -alkyl)-aminocarbonyl, cyclo-C 3-6 -alkyl-amino-carbonyl, cyclo-C 3-6 -alkyleneimino-carbonyl, phenylaminocarbonyl, cyclo-C 3-6 -alkyleneimino-C 2-4 -alkyl-aminocarbonyl, C 1-4 -alkyl-sulfonyl, C 1-4 -alkyl-sulfinyl, C 1-4 -alkyl-sulfonylamino, amino, C 1-4 -alkylamino, di-(C 1-4 -alkyl)-amino, C 1-4 -alkyl-carbonylamino, cyclo-C 3-6 -alkyleneimino, phenyl-C 1-3 -alkylamino, N-(C 1-4 -alkyl)phenyl-C 1-3 -alkylamino, acetylamino, propionylamino, phenylcarbonyl, phenylcarbonylamino, phenylcarbonylmethylamino, hydroxy-C 2-3 -alkylaminocarbonyl, (4-morpholinyl)carbonyl, (1-pyrrolidinyl)carbonyl, (1-piperidinyl)carbonyl, (hexahydro-1-azepinyl)carbonyl, (4-methyl-1-piperazinyl)carbonyl, methylenedioxy, aminocarbonylamino, or C 1-4 -alkylaminocarbonylamino,
wherein in each of the abovementioned groups and residues one or more C atoms are additionally optionally mono- or polysubstituted by F and/or one or two C atoms are independently optionally monosubstituted by Cl or Br and/or one or more phenyl rings independently optionally contain one, two, or three substituents selected from F, Cl, Br, I, cyano, C 1-4 -alkyl, C 1-4 -alkoxy, difluoromethyl, trifluoromethyl, hydroxy, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, acetylami no, aminocarbonyl, difluoromethoxy, trifluoromethoxy, amino-C 1-3 -alkyl, C 1-3 -alkylamino-C 1-3 -alkyl-, and di-(C 1-3 -alkyl)-amino-C 1-3 -alkyl and/or are optionally monosubstituted by nitro, and
the H atom of any carboxy group present or an H atom bound to an N atom are each optionally replaced by a group which can be cleaved in vivo, and
the tautomers, enantiomers, salts, and mixtures thereof,
and excluding the following compounds:
(1-{5-[5-(4-chlorophenyl)pyridin-2-ylethynyl]pyridin-2-yl}pyrrolidin-3-yl)dimethylamine,
5′-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-3-pyrrolidin-1-yl-3,4,5,6-tetrahydro-2H-[1,2′]-bipyridinyl,
1′-{5-[5-(4-chlorophenyl)pyridin-2-ylethynyl]pyridin-2-yl}-[1,3′]-bipyrrolidinyl,
{5-[5-(4-chlorophenyl)pyridin-2-ylethynyl]pyridin-2-yl}-(2-pyrrolidin-1-ylpropyl)amine,
5-(4-chlorophenyl)-2-[4-(1-methyl-2-piperidin-1-ylethoxy)phenylethynyl]pyridine,
5-(4-chlorophenyl)-2-[4-(3-piperidin-1-ylpyrrolidin-1-yl)phenylethynyl]pyridine,
5-(4-chlorophenyl)-2-{4-[2-(4-methylpiperidin-1-yl)propoxy]phenylethynyl}pyridine,
(1-{5-[5-(4-chlorophenyl)pyridin-2-ylethynyl]pyridin-2-yl}pyrrolidin-3-yl)-4-methylpiperidine,
5-(4-chlorophenyl)-2-[4-(2-methyl-2-piperidin-1-ylpropoxy)phenylethynyl]pyridine,
5-(4-chlorophenyl)-2-{4-[3-(4-methylpiperidin-1-yl)cyclohexyl]phenylethynyl}pyridine,
5-(4-chlorophenyl)-2-{4-[3-(4-methylpiperidin-1-yl)cyclohex-1-enyl]phenylethynyl}pyridine,
5-(4-chlorophenyl)-2-{4-[3-(4-methylpiperidin-1-yl)cyclopent-1-enyl]phenylethynyl}pyridine,
5-(4-chlorophenyl)-2-{4-[3-(4-methylpiperidin-1-yl)cyclopentyl]phenylethynyl}pyridine,
5-(4-chlorophenyl)-2-[4-(3-pyrrolidin-1-ylpropenyl)phenylethynyl]pyridine,
5-(4-chlorophenyl)-2-[4-(3-pyrrolidin-1-ylprop-1-ynyl)phenylethynyl]pyridine.
2 . The compound of formula (I) according to claim 1 , wherein:
R 1 and R 2 are each independently H, C 1-6 -alkyl, C 3-5 -alkenyl, C 3-5 -alkynyl, C 3-7 -cycloalkyl, hydroxy-C 3-7 -cycloalkyl, C 3-7 -cycloalkyl-C 1-3 -alkyl, (hydroxy-C 3-7 -cycloalkyl)-C 1-3 -alkyl, hydroxy-C 2-4 -alkyl, ω-NC-C 2-3 -alkyl, C 1-4 -alkoxy-C 2-4 -alkyl, hydroxy-C 1-4 -alkoxy-C 2-4 -alkyl, C 1-4 -alkoxy-carbonyl-C 1-4 -alkyl, carboxyl-C 1-4 -alkyl, amino-C 2-4 -alkyl, C 1-4 -alkyl-amino-C 2-4 -alkyl, di-(C 1-4 -alkyl)-amino-C 2-4 -alkyl, cyclo-C 3-6 -alkyleneimino-C 2-4 -alkyl, pyrrolidin-3-yl, N-(C 1-4 -alkyl)pyrrolidin-3-yl, pyrrolidinyl-C 1-3 -alkyl, N-(C 1-4 -alkyl)pyrrolidinyl-C 1-3 -alkyl, piperidin-3-yl, piperidin-4-yl, N—(C 1-4 -alkyl)piperidin-3-yl, N—(C 1-4 -alkyl)piperidin-4-yl, piperidinyl-C 1-3 -alkyl, N—(C 1-4 -alkyl)piperidinyl-C 1-3 -alkyl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, phenyl, phenyl-C, 1-3 -alkyl, pyridyl, or pyridyl-C 1-3 -alkyl, wherein one or more C atoms thereof are optionally independently mono- or polysubstituted by F, C 1-3 -alkyl or hydroxy-C 1-3 -alkyl, and/or one or two C atoms are optionally independently monosubstituted by Cl, Br, OH, CF 3 , or CN, and the phenyl or pyridyl group are optionally mono- or polysubstituted by identical or different groups R 20 , and, in the case of a phenyl group, is additionally optionally monosubstituted by nitro.
3 . The compound of formula (I) according to claim 1 , wherein:
R 1 and R 2 together with the N atom to which they are bound form a heterocyclic group which is selected from the meanings pyrrolidine, piperidine, 8-azabicyclo[3.2.1]octane, piperazine, wherein the free imine function is substituted by R 13 , and morpholine, wherein one or more H atoms may be replaced by identical or different groups R 14 , and/or the abovementioned heterocyclic groups may be substituted by one or two identical or different carbo- or heterocyclic groups Cy in such a way that the bond between the alkylene bridge and the group Cy is made via a single or double bond, via a common C atom forming a spirocyclic ring system, via two common adjacent C- and/or N atoms forming a fused bicyclic ring system, or via three or more C- and/or N atoms forming a bridged ring system.
4 . The compound of formula (I) according to claim 1 , wherein:
X is a propylene bridge independently substituted by one or more substituents selected from fluorine, chlorine, hydroxy, C 1-3 -alkyl, and cyclopropyl, wherein two alkyl substituents thereof are optionally joined together to form a C 3-6 -cycloalkyl group, or
an ethoxy or an ethyleneimino bridge, wherein the imino group thereof is optionally substituted by C 1-4 -alkyl, independently substituted by one or more substituents selected from fluorine, chlorine, C 1-3 -alkyl, and cyclopropyl, wherein two alkyl substituents thereof are optionally joined together to form a C 3-6 -cycloalkyl group, or if an alkyl group is linked to an imino group, they are optionally joined together to form a pyrrolidine or piperidine group, or
a —CH 2 —CH═CH— or —CH 2 —C≡C— bridge which is optionally independently substituted by one or more substituents selected from fluorine, chlorine, C 1-3 -alkyl, and cyclopropyl, wherein two alkyl substituents thereof are optionally joined together to form a C 3-6 -cycloalkyl group.
5 . The compound of formula (I) according to claim 1 , wherein:
Z is a single bond or ethylene; and W is a single bond.
6 . The compound of formula (I) according to claim 1 , wherein:
Y is phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, tetrahydronaphthyl, indolyl, dihydroindolyl, quinolinyl, dihydroquinolinyl, tetrahydroquinolinyl, isoquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl, benzimidazolyl, benzoxazolyl, chromanyl, chromen-4-onyl, benzothienyl, or benzofuranyl, wherein the cyclic groups thereof are optionally mono- or polysubstituted at one or more C atoms by identical or different R 20 groups, and, in the case of a phenyl ring, is optionally additionally monosubstituted by nitro, and/or is optionally substituted at one or more N atoms by R 21 .
7 . The compound of formula (I) according to claim 1 , wherein:
A is phenyl, pyridinyl, pyrimidinyl, pyrazinyl, or pyridazinyl, each optionally mono- or polysubstituted at one or more C atoms by identical or different R 20 groups, and, in the case of a phenyl ring, is optionally additionally monosubstituted by nitro.
8 . The compound of formula (I) according to claim 1 , wherein:
B is phenyl, cyclohexenyl, pyridyl, thienyl, or furanyl, wherein the cyclic groups thereof are optionally mono- or polysubstituted at one or more C atoms by identical or different R 20 groups, and, in the case of a phenyl group, is optionally additionally monosubstituted by nitro.
9 . The compound of formula (I) according to claim 1 , wherein:
B is phenyl, cyclohexenyl, pyridyl, thienyl, or furanyl,
wherein Y and A are unsubstituted or monosubstituted by R 20 , and B is optionally independently mono-, di-, or trisubstituted by R 20 , and, in the case of a phenyl ring, is optionally additionally monosubstituted by nitro.
10 . The compound of formula (I) according to claim 1 , wherein:
R 20 is F, Cl, Br, I, OH, cyano, methyl, difluoromethyl, trifluoromethyl, ethyl, n-propyl, isopropyl, amino, acetyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, n-propoxy, or isopropoxy, wherein each R 20 is identical or different.
11 . A physiologically acceptable salt of the compound according to claim 1 .
12 . A pharmaceutical formulation comprising the compound according to claim 1 and one or more physiologically acceptable excipients or inert carriers or diluents.
13 . A pharmaceutical formulation comprising the compound according to claim 2 and one or more physiologically acceptable excipients or inert carriers or diluents.
14 . A pharmaceutical formulation comprising the compound according to claim 3 and one or more physiologically acceptable excipients or inert carriers or diluents.
15 . A pharmaceutical formulation comprising the physiologically acceptable salt according to claim 11 and one or more physiologically acceptable excipients or inert carriers or diluents.
16 . The pharmaceutical formulation according to claim 12 further comprising a second active substance selected from the group consisting of active substances for the treatment of diabetes, active substances for the treatment of diabetic complications, active substances for the treatment of obesity, active substances for the treatment of high blood pressure, active substances for the treatment of hyperlipidemia or arteriosclerosis, active substances for the treatment of arthritis, active substances for the treatment of anxiety states, and active substances for the treatment of depression.
17 . The pharmaceutical formulation according to claim 13 further comprising a second active substance selected from the group consisting of active substances for the treatment of diabetes, active substances for the treatment of diabetic complications, active substances for the treatment of obesity, active substances for the treatment of high blood pressure, active substances for the treatment of hyperlipidemia or arteriosclerosis, active substances for the treatment of arthritis, active substances for the treatment of anxiety states, and active substances for the treatment of depression.
18 . The pharmaceutical formulation according to claim 14 further comprising a second active substance selected from the group consisting of active substances for the treatment of diabetes, active substances for the treatment of diabetic complications, active substances for the treatment of obesity, active substances for the treatment of high blood pressure, active substances for the treatment of hyperlipidemia or arteriosclerosis, active substances for the treatment of arthritis, active substances for the treatment of anxiety states, and active substances for the treatment of depression.
19 . The pharmaceutical formulation according to claim 15 further comprising a second active substance selected from the group consisting of active substances for the treatment of diabetes, active substances for the treatment of diabetic complications, active substances for the treatment of obesity, active substances for the treatment of high blood pressure, active substances for the treatment of hyperlipidemia or arteriosclerosis, active substances for the treatment of arthritis, active substances for the treatment of anxiety states, and active substances for the treatment of depression.
20 . A method for influencing the eating behavior of a mammal comprising administering to the mammal an effective amount of the compound according to claim 1 .
21 . A method for influencing the eating behavior of a mammal comprising administering to the mammal an effective amount of the compound according to claim 2 .
22 . A method for influencing the eating behavior of a mammal comprising administering to the mammal an effective amount of the compound according to claim 3 .
23 . A method for influencing the eating behavior of a mammal comprising administering to the mammal an effective amount of the physiologically acceptable salt according to claim 11 .
24 . A method for reducing the body weight and/or for preventing an increase in the body weight of a mammal comprising administering to the mammal an effective amount of the compound according to claim 1 .
25 . A method for reducing the body weight and/or for preventing an increase in the body weight of a mammal comprising administering to the mammal an effective amount of the compound according to claim 2 .
26 . A method for reducing the body weight and/or for preventing an increase in the body weight of a mammal comprising administering to the mammal an effective amount of the compound according to claim 3 .
27 . A method for reducing the body weight and/or for preventing an increase in the body weight of a mammal comprising administering to the mammal an effective amount of the physiologically acceptable salt according to claim 11 .
28 . A method for preventing or treating a metabolic disorder or eating disorder in a mammal comprising administering to the mammal an effective amount of the compound according to claim 1 .
29 . A method for preventing or treating a metabolic disorder or eating disorder in a mammal comprising administering to the mammal an effective amount of the compound according to claim 2 .
30 . A method for preventing or treating a metabolic disorder or eating disorder in a mammal comprising administering to the mammal an effective amount of the compound according to claim 3 .
31 . A method for preventing or treating a metabolic disorder or eating disorder in a mammal comprising administering to the mammal an effective amount of the physiologically acceptable salt according to claim 11 .
32 . The method according to claim 28 , wherein the metabolic disorder or eating disorder is obesity, bulimia, bulimia nervosa, cachexia, anorexia, anorexia nervosa, or hyperphagia.
33 . The method according to claim 29 , wherein the metabolic disorder or eating disorder is obesity, bulimia, bulimia nervosa, cachexia, anorexia, anorexia nervosa, or hyperphagia.
34 . The method according to claim 30 , wherein the metabolic disorder or eating disorder is obesity, bulimia, bulimia nervosa, cachexia, anorexia, anorexia nervosa, or hyperphagia.
35 . The method according to claim 31 , wherein the metabolic disorder or eating disorder is obesity, bulimia, bulimia nervosa, cachexia, anorexia, anorexia nervosa, or hyperphagia.
36 . A method for preventing or treating diabetes, diabetic retinopathy, diabetic neuropathy, diabetic nephropathy, insulin resistance, pathological glucose tolerance, encephalorrhagia, cardiac insufficiency, arteriosclerosis, high blood pressure, arthritis, or gonitis in a mammal comprising administering to the mammal an effective amount of the compound according to claim 1 .
37 . A method for preventing or treating diabetes, diabetic retinopathy, diabetic neuropathy, diabetic nephropathy, insulin resistance, pathological glucose tolerance, encephalorrhagia, cardiac insufficiency, arteriosclerosis, high blood pressure, arthritis, or gonitis in a mammal comprising administering to the mammal an effective amount of the compound according to claim 2 .
38 . A method for preventing or treating diabetes, diabetic retinopathy, diabetic neuropathy, diabetic nephropathy, insulin resistance, pathological glucose tolerance, encephalorrhagia, cardiac insufficiency, arteriosclerosis, high blood pressure, arthritis, or gonitis in a mammal comprising administering to the mammal an effective amount of the compound according to claim 3 .
39 . A method for preventing or treating hyperlipidemia, cellulitis, fat accumulation, malignant mastocytosis, systemic mastocytosis, emotional disorders, affective disorders, depression, anxiety, sleep disorders, reproductive disorders, sexual disorders, memory disorders, epilepsy, forms of dementia, or hormonal disorders in a mammal comprising administering to the mammal an effective amount of the compound according to claim 1 .
40 . A method for preventing or treating hyperlipidemia, cellulitis, fat accumulation, malignant mastocytosis, systemic mastocytosis, emotional disorders, affective disorders, depression, anxiety, sleep disorders, reproductive disorders, sexual disorders, memory disorders, epilepsy, forms of dementia, or hormonal disorders in a mammal comprising administering to the mammal an effective amount of the compound according to claim 2 .
41 . A method for preventing or treating hyperlipidemia, cellulitis, fat accumulation, malignant mastocytosis, systemic mastocytosis, emotional disorders, affective disorders, depression, anxiety, sleep disorders, reproductive disorders, sexual disorders, memory disorders, epilepsy, forms of dementia, or hormonal disorders in a mammal comprising administering to the mammal an effective amount of the compound according to claim 3 .
42 . A method for preventing or treating urinary incontinence, hyperactive urinary bladder, urgency, nycturia, or enuresis in a mammal comprising administering to the mammal an effective amount of the compound according to claim 1 .
43 . A method for preventing or treating urinary incontinence, hyperactive urinary bladder, urgency, nycturia, or enuresis in a mammal comprising administering to the mammal an effective amount of the compound according to claim 2 .
44 . A method for preventing or treating urinary incontinence, hyperactive urinary bladder, urgency, nycturia, or enuresis in a mammal comprising administering to the mammal an effective amount of the compound according to claim 3 .
45 . A method for treating dependencies and/or withdrawal symptoms in a mammal comprising administering to the mammal an effective amount of the compound according to claim 1 .
46 . A method for treating dependencies and/or withdrawal symptoms in a mammal comprising administering to the mammal an effective amount of the compound according to claim 2 .
47 . A method for treating dependencies and/or withdrawal symptoms in a mammal comprising administering to the mammal an effective amount of the compound according to claim 3.Join the waitlist — get patent alerts
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